Exchange - autodiscover / outlook connection

We recently upgraded to exchange 2013 and are having issues with outlook connecting. If you open up Outlook it just says "disconnected". I changed the settings to use Outlook Anywhere, and I get prompted for a username and password, but it doesn't take the credentials and continues to prompt me. OWA and ActiveSync are working with no issues. I also tried to create a new mail profile, but get "An encrypted connection to your mail server is not available" after typing in the credentials. I tried the unencrypted option as well with no luck.

We are using Outlook 2007 and 2010. We also have a few other exchange 2010 servers in the mix.

I have tried adjusting the IIS settings on the server with regards to ssl certificates and authentication and have ran multiple PS commands. I have tried to dig through IIS and event viewer logs, but can't seem to find anything. The only error that I can produce is "The autodiscover response did not return a URL for Exchanges Web Services" when running the "Test-OutlookWebServices....." command.

I am not sure if this is an issue with autodiscover, certificates, or possibly something pointing to the wrong server, etc..

On your CAS servers check the EWS virtual directory permissions are set to Anonymous, Basic, and Windows auth and Autodiscover virtual directory permissions are Anonymous and Windows Auth. Also make sure your EWS URL and URIs are correct.

Since you have 2007 and 2010 servers in the mix, I want to ask a few questions.

On which server is the mailbox housed or does this happen for all users?
Did you install your current certificate on the Exchange 2013 server and to which services did you assign it (IIS, SMTP, POP, IMAP)?
Did you modify your dns records to point to the Exchange 2013 server and in the case of the 2007 server did you create a legacy dns record?

You can view each url if you open the ECP and go to the Servers section. Select the 'virtual directories' link and click on the edit option (the pencil icon) for each one. They will have the internal (and if supported) external urls for each.

Also could your verify that the thumbprint for your Exchange certificate and http certificate for port 444 match?

In a command prompt type netsh http show sslcert and find the Certificate hash for IP:port 0.0.0.0:444. Validate that it matches the thumprint for your Exchange certificate that is bound to the IIS service.

[PS] C:\Windows\system32> Test-OutlookConnectivity -ProbeIdentity "OutlookSelfTestProbe"
WARNING: An unexpected error has occurred and a Watson dump is being generated: Object reference not set to an instance
of an object.
Object reference not set to an instance of an object.
+ CategoryInfo : NotSpecified: (:) [Test-OutlookConnectivity], NullReferenceException
+ FullyQualifiedErrorId : System.NullReferenceException,Microsoft.Exchange.Management.Tasks.TestOutlookConnectivit
y
+ PSComputerName : mail1.domain.com

On the Watson error, I did run the new-TestCasConnectivityUser script, but that didn't seem to change anything.

[PS] C:\Exchange 2013\Scripts>.\new-TestCasConnectivityUser.ps1
Please enter a temporary secure password for creating test users. For security purposes, the password will be changed r
egularly and automatically by the system.
Enter password: *********
Create test user on: mail1.domain.com
Click CTRL+Break to quit or click Enter to continue.:
UserPrincipalName: extest_f129cf97e73a4@domain.com
WARNING: Please update UseDatabaseQuotaDefaults to false in order for mailbox quotas to apply.
WARNING: The command completed successfully but no settings of 'domain.com/Users/extest_f129cf97e73a4' have been
modified.

You can enable the test user for Unified Messaging by running this command with the following optional parameters : [-UM
DialPlan <dialplanname> -UMExtension <numDigitsInDialplan>] . Either None or Both must be present.

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Glad you got it all sorted out. You will have to get the orphaned exchange server removed from the domain. I'm not certain how Exchange 2013 would handle this, but you might be able to get Exchange installed onto a computer that uses the same server name using the settings within AD to rebuild the Exchange configuration. Once that is done then you can complete the public folder migration and then remove the old server.

Ultimately though, I do not know what the state of the Exchange 2010 server is (was) when it went down and I do not know what your current data recovery strategy encompasses (and whether or not you can simply restore a virtual machine with your Exchange 2010 server's image/vhd or backup).

-saige-

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